A weekly podcast serving practical cybersecurity insights for small businesses. Each episode breaks down real threats and simple, effective strategies you can apply without big budgets or complex systems.
Through conversations with industry experts, we focus on what actually works—helping you protect your business, data, and reputation in today’s digital landscape.
Who Writes the Check? Cyber Insurance Gaps Business Owners Miss
Most cybersecurity conversations start with the attacker. This one starts with the insurer who pays the bill afterward. Amanda Martinez, Advisor at BCU Risk Advisors in Chicago, works with ultra-high-net-worth families and family offices. She sees what happens when a cyber loss hits and the coverage doesn't match what everyone assumed.
Amanda and Raffi cover why the biggest losses often start with routine decisions rather than sophisticated hacks. Examples include a wire request that looks legitimate, an assistant's inbox, or a home network shared by the whole household. They also discuss a common misconception: that a company's commercial cyber policy protects the owner's family and household. Amanda explains how coverage limits get set without anyone mapping how money actually moves, and what happens when an insurance application says "yes" to a control that's only partly in place.
The thread running through the episode is governance. Insurance, IT and leadership all have to agree on the facts, and someone has to own the program. For business owners, this is protecting the vault from both sides of the table.
7 Oct 2026
Your Dashboard Isn't Protecting You
Most business owners think they're protected because they've got dashboards, alerts, and reports telling them what's going on with their network. But seeing that something happened isn't the same as stopping it before it costs you.
This week on the Cybersecurity Cafe Podcast, we sit down with Stephen Franklin, Founder and CEO of NetWatch.AI, whose own team ran into this problem head-on while building the company's newest technology: valuable time gets lost every time a person has to manually connect an alert in one system to suspicious activity in another. That gap — between noticing something and actually stopping it — is where businesses stay exposed, even when they're confident they've checked the box on security.
Stephen's own path here wasn't conventional either. He earned his computer science degree at night while working full time, got laid off, and was recruited back by former colleagues before eventually holding a patented piece of technology built to close that exact gap.
We talk through where small businesses tend to overestimate their protection, what actually changes when a machine — not a person — connects the dots, and the one thing a business owner should do differently starting Monday morning.
19 Aug 2026
Run the Business, Don't Become It: A CFO's View on Cyber Risk
Most business owners treat cybersecurity as a technical problem — something for IT to handle. Stan Alhadeff sees it differently. As a fractional CFO with 30+ years in financial leadership and four company exits under his belt — including one at $180 million at 11x EBITDA — Stan has watched cyber risk show up in the numbers that actually matter: valuations, due diligence, and deal terms.
In this episode, Stan and Raffi dig into how buyers price cyber posture into an acquisition, what financial-viability questions every business owner should be asking their IT provider, and how to actually put a dollar figure on cyber risk instead of treating it as an abstract threat. They also tackle a question every CFO is fielding right now: is AI spend cannibalizing cybersecurity and SaaS budgets, or is it genuinely net-new investment?
Stan closes with the core idea behind his book, Run the Business, Don't Become It — a reminder that the same strategic discipline that prevents founders from getting consumed by day-to-day firefighting is exactly what protects a business's long-term value, cyber risk included.
If you've ever wondered whether your security spend is actually building enterprise value — or just checking a box — this conversation reframes the question.
12 Aug 2026
The Cyber Dividend: Why Security Pays Off Like an Investment
Most small business owners think of cybersecurity as an expense — something you pay for and hope you never need. Robert Maxwell, CEO of TGT Solutions and author of Cyber Model Dividends, sees it differently: as an investment that compounds over time, much like a portfolio.
After nearly three decades running a systems integration firm serving small and mid-sized businesses, Maxwell has watched the same pattern play out again and again — a company runs on one person, one account, one set of credentials, and never questions it until a single phishing email or compromised login brings the whole operation to a halt in minutes. His core argument isn't really about technology at all. It's about cash flow, client trust, and business continuity — the things an SME actually stands to lose, and the reason most owners don't think they're a target until it's already too late.
In this conversation, we dig into that reframe: why treating cybersecurity like a dividend-generating asset changes the decisions owners make, what a single point of failure looks like inside a real business, and the smallest, cheapest steps that actually move the needle — no jargon, no fear-selling.
Link to book: Cyber Model Dividends (https://a.co/d/0b4et2JO)
5 Aug 2026
When Change becomes Risk
Aimee Ritell is Founder & Principal of Intwinely, a Fractional COO who steps into SMBs to diagnose operational bottlenecks driving employee/client churn, typically starting with a flat-fee discovery assessment. In this episode we dive into what leads to employee and client churn and if its avoidable or invevitable.
29 Jul 2026
AI security hype, remediation capacity, and what mid-market leaders actually need
Mike Reed has seen cybersecurity from every angle — launching Exchange and Active Directory at Microsoft, early enterprise at Apple, leading the managed-security ISV business at AWS, and serving as a Field CISO at Fortra before co-founding Realis Solutions Group, a boutique AI and emerging-risk advisory. That builder-and-practitioner background makes him one of the few voices who can separate genuine capability from vendor marketing.
In this episode, we dig into his clear-eyed take on Anthropic's Claude Mythos and Project Glasswing — why AI that finds vulnerabilities faster than anyone can patch them doesn't automatically make you safer, and why "the limiting factor isn't model access, it's remediation capacity." We also get into the security metrics leadership will actually act on, how a mid-market firm should think about state-sponsored threats without falling for FUD, and what MSPs and CISOs each get wrong about the other.
22 Jul 2026
From Enterprise to Independent
After nearly two decades in financial services — including nine years at Charles Schwab and a background in algorithmic and statistical-arbitrage trading — Emil Aldaddah left the enterprise world in 2024 to co-found Momentum Wealth Management, a boutique SEC-registered RIA serving family offices, trustees, and private foundations. On this episode, Emil and Raffi cover what disappears when you walk away from a major platform's security and compliance infrastructure, the unique threat profile of UHNW and family-office clients, advisor-impersonation wire fraud, and how the new SEC cybersecurity rules landed squarely on his launch timeline.
15 Jul 2026
Secure Isn't Defensible — A Former SEC Examiner on What Actually Gets You Flagged
A former SEC enforcement director on the difference between being secure and being defensible. Ana Petrovic (Kroll) on what examiners really look for, how infosec became an insider-trading control, and where a lean firm should spend its next compliance dollar.
17 Jun 2026
Security Through an Investor's Eyes
Most cybersecurity conversations happen with practitioners—the people building and defending the systems. This one is different. Jeffrey Fidelman, CEO and Founder of Fidelman & Company, sits on the other side of the table:, the one with the checks.
With a background at Morgan Stanley and HSBC and a firm that helps startups and emerging funds raise capital, Jeffrey brings an investor's lens to security. We dig into how cybersecurity actually shows up in due diligence, what a company's security posture signals to a serious investor, and the gaps that quietly kill deals. He explains why founders who frame security as a cost center may be hurting their own fundraise—and how to talk about it as an asset instead.
6 May 2026
Security is a progress not a purchase
Most business leaders approach cybersecurity the way they approach every other operational problem: buy the right tool, check the box, move on. It's a reasonable instinct — and in most areas of business, it works. But cybersecurity doesn't behave like other purchases, and the companies that learn this the hard way usually learn it during a client questionnaire, an insurance renewal, or an incident they weren't prepared for. In this solo episode, we dig into why the purchase mindset feels so right — and why it consistently falls short. You'll hear why a tool isn't a control until it's configured, monitored, and owned. Why static security is decaying security. And why the right question isn't "are we secure?" but "are we improving — and can we demonstrate it? "We'll walk through what continuous improvement actually looks like in practice, the rhythm of a mature security program, and the clear signs that tell you whether your organization is in process mode or still stuck in purchase mode. You'll also get five diagnostic questions every leader should be able to answer about their security program. If you can't answer them quickly, you have a starting point. If you can, you're already ahead of most of your peers. Whether you run a five-person firm or a five-hundred-person company, this episode is about shifting how you think about security — from something you buy to something you practice.
16 Apr 2026
Business Adoption of AI
In this episode of the podcast we talk to Bobby Tahir. Bobby has a broad knowledge of technology as a multi-company CTO both for Private Equity and their Portfolio Companies. Bobby has a blog and podcast at Technocratic | Substack (https://newsletter.technocratic.io/)
1 Apr 2026
Incident Response Planning
In this episode we talk about responding to an incident response process. We talk to Chris Loehr, a leading incident responder.
25 Mar 2026
Protecting Customer Data
We work on protecting our computers, mobile phones and even our accounts with MFA, but we forget about how to project the actual data.
25 Mar 2026
Human Vulnerabilities
We discuss human vulnerabities, security awareness and more.
25 Mar 2026
Ep1 - Intro
This is our initial introduction video
Reach and audience
Public platform figures. Ratings count people who left a rating, not total listeners.
Apple Podcasts (US)
5.0 / 5
1 ratings
Host of Cyber Security Cafe?
Claim your podcast to manage its listing and keep your show details accurate.
Pod Engine is an independent podcast discovery and analytics service and is not affiliated with or endorsed by this podcast. Artwork and show content belong to their owners. Full legal notice.
Explore this show Podcast research with Pod Engine
